Were looking for a

Director, Product Management

Director, Product Management — Learning

About Cornerstone:

Cornerstone powers the future of work by helping organizations develop, engage, and grow their people. Our learning and talent platform serves thousands of organizations and millions of learners worldwide, bringing together learning experiences, skills intelligence, content, and analytics so people can build the capabilities their organizations need most. We are investing heavily in the next generation of learning — including AI-assisted, skills-based, and outcome-driven experiences — and we are looking for product leaders who can turn that ambition into products customers love.

About the Role:

Cornerstone is seeking a Director of Product Management to lead a core area of our Learning product line. This is a senior product leadership role that combines product vision and strategy, people leadership, and disciplined execution. You will own the strategy and roadmap for your area, lead and grow a team of product managers, and be accountable for delivering learning experiences that drive measurable adoption, learner and administrator value, and commercial impact.

You will partner across engineering, design, data science, content, customer success, services, sales, and marketing to move capabilities from customer need through discovery, launch, adoption, and outcome realization. The ideal candidate brings deep enterprise SaaS product experience, a strong track record building products that customers adopt and love, and the judgment to balance long-term platform strategy with the operational rigor required to ship. Experience with AI-native and skills-based capabilities is a strong plus — AI is an increasingly central theme across the Learning portfolio.

In this role you will...

Set vision & strategy

• Own the product vision and multi-year roadmap for your area of the Learning portfolio, grounded in market trends, customer needs, and Cornerstones strategy.
• Make and defend prioritization decisions with clear rationale, translating strategy into a sequenced roadmap and well-formed bets.
• Frame the business case for major investments — market sizing, opportunity, and expected outcomes — and align leadership and cross-functional partners behind it.
• Champion AI and skills-based innovation where it creates real learner and administrator value, integrating intelligent capabilities responsibly into the learning experience.

Lead & grow the team

• Hire, coach, and develop a team of product managers, setting a high bar for product craft, customer empathy, and accountability.
• Establish product standards and operating cadences for discovery, planning, release, and outcome review across your team.
• Create clarity and alignment across product, engineering, and design leadership, and represent your area to executives and customers.

Discover, experiment & measure

• Drive rigorous customer discovery, engaging directly with enterprise customers, learners, and administrators to validate problems and use cases before committing to solutions.
• Run a hypothesis-driven practice — define success metrics, instrument products, and use experimentation and A/B testing to learn quickly and de-risk decisions.
• Define and own the success metrics and North Star for your area (adoption, engagement, retention, time-to-value, and business outcomes), and use them to guide investment.
• Translate customer, field, and market feedback into clear requirements, prioritized backlogs, and release plans.

Deliver with rigor

• Drive cross-functional delivery across product, engineering, design, data science, content, customer success, services, and go-to-market teams.
• Establish strong operating cadences for milestone reviews, dependency management, risk tracking, and outcome measurement, surfacing risks early.
• Partner with go-to-market and customer-facing teams on rollout planning, launch enablement, implementation readiness, and feedback loops.
• Ensure capabilities are scalable, secure, compliant, and practical for adoption in enterprise environments, meeting expectations for security, privacy, and data governance.

What Success Looks Like:

• A clear, well-communicated vision and roadmap that leadership, customers, and the team understand and rally behind.
• A high-performing product team that ships quality work on a predictable cadence and grows in capability.
  Products that customers adopt and love — reflected in faster time-to-value, stronger engagement and retention, anD measurable business outcomes.
• Decisions grounded in evidence from discovery, experimentation, and metrics rather than opinion alone.
• AI-assisted and skills-based capabilities launched in ways that are trusted, usable, and outcome-oriented.
• Security, compliance, and data governance requirements embedded into delivery from the start.

Youve got what it takes if you have…

• 10+ years in product management, including experience leading product managers, in enterprise software, SaaS, or platform organizations.
• A track record of owning product vision and strategy for a product area and translating it into roadmaps that ship and drive outcomes.
• Demonstrated people leadership — hiring, coaching, and growing product managers and setting team standards.
• Strong discovery and experimentation skills: customer research, hypothesis-driven development, metrics definition, and A/B testing.
• Proven ability to lead execution across complex cross-functional organizations with operational rigor and release discipline.
• Excellent collaboration and communication skills across engineering, UX, data science, services, sales, support, and customer success, up to the executive level.
• Experience delivering products in secure, enterprise-grade environments where trust, reliability, and scalability matter, including familiarity with security, privacy, and data governance.

Nice to Have:

• Experience in learning, HR technology, talent management, or skills/EdTech domains.
• Experience delivering AI-native products, intelligent agents, copilots, automation, or workflow-based AI in enterprise settings.
• Experience with skills-based capabilities, content ecosystems, or analytics/insights products.
• Familiarity with regulated, security-conscious, or compliance-driven product environments and enterprise governance models for AI and data.

#LI-Onsite

Our Culture:

Spark Greatness. Shatter Boundaries. Share Success. Are you ready? Because here, right now – is where the future of work is happening. Where curious disruptors and change innovators like you are helping communities and customers enable everyone – anywhere – to learn, grow and advance. To be better tomorrow than they are today.  

Who We Are:

At Cornerstone, we believe in AI that works in the service of people, amplifying their judgment to drive high-performing, future-ready organizations forward. Cornerstone Workforce AI™, the intelligence platform for workforce readiness, brings together workforce and labor market data into a proprietary Cornerstone People Graph™, translating signals into intelligence, targeting learning where it matters, developing critical skills, and surfacing hidden talent. Delivered as an open, enterprise platform across whatever application your people work in every day, Cornerstone Workforce AI is built for scale, security, and trust, with certified AI guardrails. As an industry leader, Cornerstone is helping approximately 7,000 organizations, 140M+ users, across 186 countries build continuous workforce readiness.

Check us out on LinkedIn, Comparably, Glassdoor, and Facebook!